Pyrido[3,4-b]indole-6-carboxylic acid compounds as CK2 inhibitors

Abstract

Novel pyrido[3,4-b]indole-6-carboxylic acid compounds, a method of synthesizing said compounds, a pharmaceutical composition comprising said compounds and a suitable carrier, and a method of using the compounds. The pyrido[3,4-b]indole-6-carboxylic acid compounds, identified as CK2 inhibitors, are useful as anticancer and/or antitumor agents, and as agents for treating other kinase-associated conditions including inflammation, pain, and certain immunological disorders, and other types of diseases such as diabetes, viral infection, neurodegenerative diseases.

We claim: 
     
       1. A compound having the formula I: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable ester, stereoisomer, or solvate thereof, wherein:
 R 1  is hydrogen or a C 1 -C 6  straight or branched chain alkyl; 
 R 2  is a —COphenyl group substituted with:
 i) one or two chlorine atoms, 
 ii) —CON(CH 3 ) 2 , or 
 iii) methyl. 
 
 
       
     
     
       2. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the compound of  claim 1  and a pharmaceutically acceptable carrier. 
     
     
       3. A compound having the formula I: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable ester, stereoisomer, or solvate thereof, wherein:
 R 1  is hydrogen; and 
 R 2  is a —COphenyl group substituted with:
 i) one or two chlorine atoms, 
 ii) —CON(CH 3 ) 2 , or 
 iii) methyl. 
 
 
       
     
     
       4. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the compound of  claim 3  and a pharmaceutically acceptable carrier. 
     
     
       5. A compound selected from the group consisting of:
 9-(3-chlorobenzoyl)-9H-pyrido[3,4-b]indole-6-carboxylic acid (7), 
 9-(3-(dimethylcarbamoyl)benzoyl)-9H-pyrido[3,4-b]indole-6-carboxylic acid (8), 
 9-(3,5-dichlorobenzoyl)-9H-pyrido[3,4-b]indole-6-carboxylic acid (9), 
 9-(3-methylbenzoyl)-9H-pyrido[3,4-b]indole-6-carboxylic acid (10), 
 and a pharmaceutically acceptable ester, stereoisomer, or solvate thereof. 
 
     
     
       6. A pharmaceutically acceptable composition comprising a therapeutically effective amount of the compound of  claim 5  and a pharmaceutically acceptable carrier.